Interview: Comic Pete Holmes talks about his new late-night talk show

Pete Holmes has one guest at the top of his wishlist for his new late-night talk show.

“I’m looking at a picture of Gosling right now,” laughs Holmes, calling from his office in Los Angeles. “I’m not joking. I have a still from Drive in the office. We are out to Gosling, and I can certainly say that he’s the biggest get for me. And if he reads this, Daddy Gos, please, make our dreams come true.”

Holmes may not be a household name, but there’s not much that his fans don’t already know about him — his fascination with Ryan Gosling, his obsession with spirituality, how his marriage dissolved when his wife had an affair, how he lost his virginity in, as he puts it, “six pumps.” He’s laid every facet of himself bare on his podcast, You Made It Weird, a series of deep, lengthy and remarkably candid conversations about comedy, sex and religion with pals and fellow stand-ups like Jon Hamm, Zach Galifianakis, Aziz Ansari and Dane Cook.
Now Holmes — whose most prominent TV credit to date is the voice of the E-trade baby — is bringing his big, boisterous personality to late-night TV. The Pete Holmes Show will premiere at midnight Monday on TBS, following Conan. Conan O’Brien’s company is producing the show, which for Holmes is a dream come true.

“I had a weird fascination with Conan,” Holmes said. “I always wanted to gain his approval. I remember one time talking about it on stage: 'I just want to jump ahead to Conan telling me that I’m hilarious.’ And no one laughed, because why would you laugh? That’s an unrelatable thought. Nobody understands what you’re talking about. ... The literal dream-come-true of it all is pretty storybook and hard to wrap my brain around. He was the stick that I measured myself by; he was the benchmark.”

We asked Holmes to walk us through the process of starting a late-night talk show from scratch, and when he called recently to chat, for a brief second, his voice threw us for a loop.

I wasn’t expecting you to call directly. I was expecting someone else would call and you’d be looped in.Nah, I can’t be looped in. I’m a man of the people. Can that be the headline? (laughs)

That can be the headline if I can also include the line, “Can that be the headline?”(laughs) Did you ever watch the British Office, where Ricky Gervais gets interviewed, and he keeps saying, “...Brent mused...” like he’s telling her what to write?

When you found out you were getting a talk show, did you just wipe the whiteboard clean and start from scratch? Or did you consider all the elements of a traditional talk show and try to think about how to fit your personality into them?We’re really trying to make a show that’ll stand out, that’ll be different, and there have been different phases of the development where we’ve been like, “What if there isn’t an interview?” or “What if the interview’s first, and the monologue’s at the end?” Ultimately, we decided that me being myself would make the show unique, and then we started to tinker and tool around with each traditional act and see how we could change it to make it more like my sensibility.

Host aside, in your mind, what’s the most important element of a late-night talk show?Authenticty. Authenticity and transparency are the two things we’re going for. We don’t want to do anything fake. I don’t want to say anything I don’t actually feel. I don’t want to write a monologue joke that I’m not really behind. I don’t want to have a guest I don’t really care about. And also, we don’t know what we’re doing — we want to be open about that. If we’re playing with the idea of, for one episode, having a sidekick, just to see how it is, we’ll be open about the fact that that’s what we’re playing with and letting the audience in on the development, so it kind of feels like our show rather than us imposing a show on the audience. Seeing what works, seeing what sticks.

To the point of authenticity: Have you decided yet whether you’re going to do pre-interviews? Or are you going to try to keep it loose, like on the podcast?I really want to keep it as loose as possible. We’re going to overshoot the interview portion. I/d like it to be a little less rehearsed and a little more familiar. We don’t have the guests nailed down quite yet, but I would like it to be a lot of the people that I’m familiar with that are actually friends of mine, because I happen to be friends with some of the most talented and wonderful comedians in the country, and that sort of thing, that you can’t fake.

A podcast listener would know the backstory and relationship you have with, say, Chelsea Peretti or John Mulaney, but splashing that on a national TV audience without any sort of explanation, people might be wondering, “What’s going on here?” How do you balance the people who know WAY too much about you with the people who know nothing about you?Yeah, there’s going to have to be some repetition there. The diehard podcast fan is going to know some of the stuff we’ll be revealing to a much bigger audience, for sure. We’re not assuming you’ve heard the podcast; we’re not assuming you know who John Mulaney or Kumail (Nanjiani) is. But we’re going to slowly bring the audience into them the way that we have with the podcast. It’s going to take time, but I hope once it’s done, the TV show will have that sort of communal feel, where if you’re watching the show and you’re invested in the show, you will have that clubhouse mentality, where it’s like, “We know who these people are. These are the characters.”

Was there a moment in the run of the podcast where you thought, You know, we could do this on TV and people might watch?Yeah, a little bit, certainly. When we went to Turner and pitched the show, I said that I felt like it already existed; it had just been broken into five different bits. The interview was certainly one of them. And when people at Conaco and people at TBS listen to the interviews, I think they did latch onto the idea that it was a little bit of a different style, and we were going different places, just by virtue of what I’m interested in. So that — being what I would think is an underrepresented interview style — would be fun to see how much of that feel we can capture, certainly.

Since you’re going to be on TV, are there things that you’ve revealed about yourself on the podcast that you now think, 'I kind of wish that wasn’t out there.'(laughs) That hasn’t happened yet. I think I’m going to have to have a wife and kids for that to happen. But so far, the intention is to keep that oversharing mentality. Because that intimacy and regularity that I have with the audience — twice a week, spending a couple of hours talking to my friends and having these people listening in and learning about you — really does create a pretty close bond between the performer and the audience, and I’d like to continue that with the TV show. So in the pilot and some of the stuff that we’ve already shot, there’s references to being divorced, there’s references to losing my virginity in six pumps, there’s references to the fact that I see a hypnotherapist, or whatever I might be trying at the time. I’d like to see if we can not have the host be this polished person, but a fallible doofus, which is what I am.

Midnight isn’t virgin territory, but it’s also not 12:35 or 11:35. To me, it’s hard to know if there’s a sensibility that screams midnight. Can you define the type of humor that works at midnight or later?When I think about it, I always go back to early Conan and early Letterman — that sort of, “No one’s watching, we have no budget...” I think a lot of those shows, even popular shows, still go with the “no one’s watching and we have no budget” angle. But with us, literally, very few people might be watching at first, and we might not have a budget. (laughs) I’m not saying I have low expectations for the show, but when you’re on at midnight, there’s a better chance that we can get away with some stuff. Maybe we can do some things that you can’t get away with at an earlier timeslot.

I’m sure you watched a lot of Conan at 12:35, but did you watch much of Late Night with David Letterman?I did. Letterman was one of the first live tapings I went to when I was a kid, because I loved him. I didn’t get to stay up as late as I would have liked, but I was certainly aware of him and was a fan of him. The kind of serial, habitual watching of a late night show did start for me with Conan, especially because I lived in Chicago when I was 22, so he would be on an hour earlier, and it was even easier to catch him every night.

Conan, like you, has this big, boisterous stage persona. But both he and Letterman had this knack for really subversive, meta, intellectual humor, and yours is so personality-driven. It’s very different from what Letterman brought to the table. Do you think your show is in line with those shows? Or is there another show that you think The Pete Holmes Show has as an ancestor?I get little glimpses of what this show might be. Hopefully it will be a new thing. It’ll be informed by Conan and Letterman, but I agree with you — there is something different happening here. And when you say it’s my personality, I’m glad, because I’m the only one with this exact personality, and the more I can represent it, the more this show can be unique. One of my favorite quotes is Bill Hicks saying, “If you’re yourself, no one can be you as well as you can be, so you’ll have supply and demand covered.” That’s definitely what we’re going for here. I’m not trying to mimic Conan. Hopefully when people watch this, they will go, “This is something new, this is something we haven’t seen before. This isn’t necessarily a subversive or sarcastic Letterman approach, and it’s not that exact same Conan goofienss. This is some new kind of idiot.”

Are there bits you recall not just from Late Night with Letterman or Conan, but any other late night show that you play back in your head when you’re thinking about what you want your show to be?I’ve watched a fair share of best of The Tonight Show, best of Conan, best of Letterman. But the stuff that I really, really absorb is the interviews with them. I love the Charlie Rose interviews with Letterman, I love the Charlie Rose interview with Conan, I love the Inside the Actors Studio with Conan. If you want to get into my late-night mission statements, or if you want to hear the way that I talk to the staff, you’ll hear me pulling quotse about what Conan said about his early years, what Letterman said about his early years, more than I’ll reference Masturbating Bear or Will It Float? or the velcro suit or anything like that. I absorb the ideologies more than the bits themselves. Now, I can actually go talk to Conan and have these talks about what it’s like to start and get that advice in real time. So that’s incredible as well.